Abstract
5-Phenyl-2-phenylimino-4-oxazolidinone exists in DMSO-D6 in the form of a mixture of the E and Z isomers of the imino tautomer, but it crystallizes in the amino form. Parallelism between the basicity and nucleophilicity of the reaction centers of this mesomeric anion is observed when the alternative isomers (and the tautomers corresponding to them) differ significantly in stability. If this condition is not fulfilled, these parameters do not coincide, as is illustrated in the example of its methylation reaction.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature Cited
G. Rapi, M. Ginanneschi, E. Belgodere, and M. Chelli, J. Heterocycl. Chem., 9, 285 (1972).
C. R. Howell, N. Q. Quinones, and R. A. Hardy, J. Org. Chem., 27, 1686 (1962).
C. F. Howell, W. Fulmor, N. Q. Quinones, and R. A. Hardy, J. Org. Chem., 29, 370 (1964).
S. M. Ramsh, N. A. Smorygo, E. S. Khrabrova, and A. I. Ginak, Khim. Geterotsikl. Soedin., No. 4, 544 (1986).
S. M. Ramsh, N. A. Smorygo, and A. I. Ginak, Khim. Geterotsikl. Soedin., No. 8, 1066 (1984).
L. Pauling and P. Pauling, Chemistry, Freeman, San Francisco (1975).
S. M. Ramsh, N. A. Smorygo, and E. S. Khrabrova, Khim. Geterotsikl. Soedin., No. 1, 32 (1985).
S. A. Shevelev, Usp. Khim., 39, 1773 (1970).
D. J. Cram, Fundamentals of Carbanion Chemistry, Academic Press, New York (1965).
S. M. Ramsh, A. I. Ginak, N. A. Smorygo, Yu. G. Basova, and E. G. Sochilin, Zh. Org. Khim., 14, 1327 (1978).
S. M. Ramsh, E. S. Khrabrova, A. I. Ginak, and G. B. Erusalimskii, Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol., 29, 33 (1986).
R. F. Hudson, “Nucleophilic reactivity,” in: G. Klopman (ed.), Chemical Reactivity and Reaction Paths, Wiley, New York (1974), pp. 167–252.
B. C. Challis, J. N. Iley, and H. S. Rzepa, J. Chem. Soc., Perkin Trans II, No. 7, 1037 (1983).
S. M. Ramsh, A. I. Ginak, Yu. G. Basova, and L. P. Shamina, Zh. Org. Khim., 17, 846 (1981).
G. Klopman, “The generalized perturbation theory of chemical reactivity and its applications,” in: G. Klopman (ed.), Chemical Reactivity and Reaction Paths, Wiley, New York (1974), pp. 55–165.
T. I. Temnikova and S. N. Semenova, Molecular Rearrangements in Organic Chemistry [in Russian], Khimiya, Leningrad (1983).
Yu. G. Basova, S. M. Ramsh, and A. I. Ginak, Zh. Org. Khim., 18, 2200 (1982).
Yu. G. Basova, S. M. Ramsh, A. I. Ginak, and A. E. Karpovich, Zh. Org. Khim., 18, 2205 (1982).
Yu. G. Basova, S. M. Ramsh, and A. I. Ginak, Zh. Org. Khim., 17, 663 (1981).
Yu. G. Basova, Dissertation for the degree of Candidate of Chemical Sciences, Leningrad (1980).
S. Shinkai, T. Fukunaga, O. Manabe, and T. Kunitake, J. Org. Chem., 44, 4990 (1979).
S. M. Ramsh, A. I. Ginak, Yu. G. Basova, and L. P. Shamina, Zh. Org. Khim., 17, 851 (1981).
General Organic Chemistry, Vol. 5, Phosphorus and Sulfur Compounds [in Russian], Khimiya, Moscow (1983).
S. M. Ramsh, N. A. Smorygo, A. I. Ginak, and E. G. Sochilin, Zh. Org. Khim., 15, 1506 (1979).
H. Aspelund, Acta Acad. Aboensis. Mat. Phys., 26, No. 8, 1 (1967).
W. Traube and R. Ascher, Berichte, 46, 2077 (1913).
C. F. Howell, N. Q. Quinones, and R. A. Hardy, J. Org. Chem., 27, 1679 (1962).
H. Aspelund, Acta Acad. Aboensis. Mat. Phys., 26, No. 11, 1 (1967).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 388–392, March, 1989.
Rights and permissions
About this article
Cite this article
Ramsh, S.M., Khrabrova, E.S. & Ginak, A.I. Structure and dual reactivity of 2-phenylpemoline. Chem Heterocycl Compd 25, 325–329 (1989). https://doi.org/10.1007/BF00472395
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF00472395